Stanozolol

Identification

Summary

Stanozolol is an anabolic steroid used to manage hereditary angioedema.

Generic Name
Stanozolol
DrugBank Accession Number
DB06718
Background

Stanozolol is a synthetic anabolic steroid with therapeutic uses in treating hereditary angioedema. Stanozolol is derived from testosterone, and has been abused by several high profile professional athletes.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Thumb
Weight
Average: 328.4916
Monoisotopic: 328.251463656
Chemical Formula
C21H32N2O
Synonyms
  • Androstanazol
  • Androstanazole
  • Estanozolol
  • Stanozolol
External IDs
  • NSC-43193
  • WIN 14833

Pharmacology

Indication

Stanozolol is a synthetic anabolic steroid with therapeutic uses in treating C1-inhibitor deficient hereditary angioedema. C1-inhibitor is a protease that inhibits the complement system (part of the innate immune system), a biochemical chain of reactions which assists the body in removing pathogens from the body. Stanozolol may help control attacks of hereditary angioedema. Stanozolol can be administered orally or intramuscularly.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Stanozolol is a synthetic anabolic-androgenic steroid (AAS), which promotes cell growth (anabolism) and development/maintenance of masculine characteristics (androgenism).

Mechanism of action

Stanozolol binds to androgen receptors, such as membrane bound receptor proteins LAGS and stanozolol-binding protein (STBP).

TargetActionsOrganism
AAndrogen receptor
agonist
Humans
UGlucocorticoid binding proteins
binder
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

24 hours

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseStanozolol may increase the hypoglycemic activities of Acarbose.
AcenocoumarolStanozolol may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideStanozolol may increase the hypoglycemic activities of Acetohexamide.
AlbiglutideStanozolol may increase the hypoglycemic activities of Albiglutide.
AllantoinThe therapeutic efficacy of Allantoin can be increased when used in combination with Stanozolol.
AlogliptinStanozolol may increase the hypoglycemic activities of Alogliptin.
Beclomethasone dipropionateThe risk or severity of fluid retention can be increased when Beclomethasone dipropionate is combined with Stanozolol.
BetamethasoneThe risk or severity of fluid retention can be increased when Betamethasone is combined with Stanozolol.
Betamethasone phosphateThe risk or severity of fluid retention can be increased when Betamethasone phosphate is combined with Stanozolol.
BromocriptineStanozolol may increase the hypoglycemic activities of Bromocriptine.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Stromba / Winstrol / Winstrol Depot

Categories

ATC Codes
A14AA02 — Stanozolol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrane steroids
Alternative Parents
17-hydroxysteroids / Tertiary alcohols / Pyrazoles / Heteroaromatic compounds / Cyclic alcohols and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Cyclic alcohol / Estrane-skeleton / Heteroaromatic compound / Hydrocarbon derivative / Hydroxysteroid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary alcohol, organic heteropentacyclic compound, 17beta-hydroxy steroid, anabolic androgenic steroid (CHEBI:9249) / Androstane and derivatives (C07311)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
4R1VB9P8V3
CAS number
10418-03-8
InChI Key
LKAJKIOFIWVMDJ-IYRCEVNGSA-N
InChI
InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1
IUPAC Name
(1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=NNC=C3C[C@]12C

References

General References
  1. Guilarte M, Luengo O, Nogueiras C, Labrador-Horrillo M, Munoz E, Lopez A, Cardona V: Acquired angioedema associated with hereditary angioedema due to C1 inhibitor deficiency. J Investig Allergol Clin Immunol. 2008;18(2):126-30. [Article]
  2. Thevis M, Schanzer W: Synthetic anabolic agents: steroids and nonsteroidal selective androgen receptor modulators. Handb Exp Pharmacol. 2010;(195):99-126. doi: 10.1007/978-3-540-79088-4_5. [Article]
  3. Sloane DE, Lee CW, Sheffer AL: Hereditary angioedema: Safety of long-term stanozolol therapy. J Allergy Clin Immunol. 2007 Sep;120(3):654-8. [Article]
Human Metabolome Database
HMDB0003116
KEGG Drug
D00444
KEGG Compound
C07311
PubChem Compound
25249
PubChem Substance
99443270
ChemSpider
23582
RxNav
10032
ChEBI
9249
ChEMBL
CHEMBL2079587
ZINC
ZINC000004097376
PharmGKB
PA165958391
Wikipedia
Stanozolol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3Not Yet RecruitingTreatmentMDS1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule10 mg
Tablet10 mg
Capsule5 mg
Tablet5 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00173 mg/mLALOGPS
logP4.33ALOGPS
logP3.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.23ChemAxon
pKa (Strongest Basic)2.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.91 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity96.8 m3·mol-1ChemAxon
Polarizability39.22 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9745
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6928
P-glycoprotein inhibitor INon-inhibitor0.7667
P-glycoprotein inhibitor IINon-inhibitor0.8443
Renal organic cation transporterNon-inhibitor0.7071
CYP450 2C9 substrateNon-substrate0.792
CYP450 2D6 substrateNon-substrate0.7667
CYP450 3A4 substrateSubstrate0.6765
CYP450 1A2 substrateInhibitor0.5646
CYP450 2C9 inhibitorNon-inhibitor0.5135
CYP450 2D6 inhibitorNon-inhibitor0.8852
CYP450 2C19 inhibitorInhibitor0.6303
CYP450 3A4 inhibitorInhibitor0.6272
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5576
Ames testNon AMES toxic0.6989
CarcinogenicityNon-carcinogens0.8476
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5131 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9218
hERG inhibition (predictor II)Non-inhibitor0.6182
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Gao W, Bohl CE, Dalton JT: Chemistry and structural biology of androgen receptor. Chem Rev. 2005 Sep;105(9):3352-70. doi: 10.1021/cr020456u. [Article]
  2. Saartok T, Dahlberg E, Gustafsson JA: Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin. Endocrinology. 1984 Jun;114(6):2100-6. doi: 10.1210/endo-114-6-2100. [Article]
  3. Holterhus PM, Piefke S, Hiort O: Anabolic steroids, testosterone-precursors and virilizing androgens induce distinct activation profiles of androgen responsive promoter constructs. J Steroid Biochem Mol Biol. 2002 Nov;82(4-5):269-75. [Article]
  4. Compound report card: Stanozolol [Link]
2. Glucocorticoid binding proteins
Kind
Group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Curator comments
Glucocorticoid binding proteins includes low-affinity glucocorticoid binding proteins (LAGS) and stanozolol binding proteins (STBP) are included as targets for this drug.
A group of glucocorticoid binding proteins in humans, including low-affinity glucocorticoid binding proteins (LAGS) and stanozolol binding protein (STBP).
References
  1. Betancor-Hernandez E, Perez-Machin R, Henriquez-Hernandez L, Mateos-Diaz C, Novoa-Mogollon J, Fernandez-Perez L: Photoaffinity labeling identification of thyroid hormone-regulated glucocorticoid-binding peptides in rat liver endoplasmic reticulum: an oligomeric protein with high affinity for 16beta-hydroxylated stanozolol. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):253-64. [Article]
  2. Lippman ME, Halterman RH, Leventhal BG, Perry S, Thompson EB: Glucocorticoid-binding proteins in human acute lymphoblastic leukemic blast cells. J Clin Invest. 1973 Jul;52(7):1715-25. doi: 10.1172/JCI107353. [Article]
  3. Fernandez L, Chirino R, Boada LD, Navarro D, Cabrera N, del Rio I, Diaz-Chico BN: Stanozolol and danazol, unlike natural androgens, interact with the low affinity glucocorticoid-binding sites from male rat liver microsomes. Endocrinology. 1994 Mar;134(3):1401-8. doi: 10.1210/endo.134.3.8119180. [Article]

Drug created on May 17, 2010 18:57 / Updated on June 19, 2021 00:26